1-O-(8-O-tosyloctanoyl)-2-O-palmitoyl-3-O-trityl-rac-glycerol | 314057-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-O-(8-O-tosyloctanoyl)-2-O-palmitoyl-3-O-trityl-rac-glycerol
• 英文别名: 2-O-palmitoyl-1-O-(8-O-tosyloctanoyl)-3-O-trityl-rac-glycerol；[1-[8-(4-Methylphenyl)sulfonyloxyoctanoyloxy]-3-trityloxypropan-2-yl] hexadecanoate
• CAS: 314057-88-0
• 化学式: C₅₃H₇₂O₈S
• 分子量: 869.216
• InChiKey: LUHQSFNRXHULDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.4
• 重原子数：
  62
• 可旋转键数：
  35
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-O-(8-O-tosyloctanoyl)-2-O-palmitoyl-3-O-trityl-rac-glycerol 在 potassium fluoride 、 18-冠醚-6 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以82%的产率得到1-O-(8-fluorooctanoyl)-2-O-palmitoyl-3-O-trityl-rac-glycerol
  参考文献：
  名称：

  Synthesis of 1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol for imaging intracellular signal transduction

  摘要：

  An improved approach to the synthesis of 1-O-(8-[F-18]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol (rac-1,2-[F-18]FDAG) has been developed. We designed and synthesized two new types of precursors for the radiosynthesis and investigated their general utility. Each precursor was smoothly radiofluorinated (5 min) and the protecting soup at the 3-O-position was rapidly removed (1 min). The resulting rac-1,2-[F-18]FDAG was obtained in overall radiochemical yields of 20-30% (EOB) within 70 min including final preparative HPLC separation.

  DOI：

  10.1002/1099-1344(20001030)43:12<1159::aid-jlcr402>3.0.co;2-z
• 作为产物：
  描述：

  8-溴辛酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 Amberite IR 120(+) 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 178.75h， 生成 1-O-(8-O-tosyloctanoyl)-2-O-palmitoyl-3-O-trityl-rac-glycerol
  参考文献：
  名称：

  Synthesis of 1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol for imaging intracellular signal transduction

  摘要：

  An improved approach to the synthesis of 1-O-(8-[F-18]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol (rac-1,2-[F-18]FDAG) has been developed. We designed and synthesized two new types of precursors for the radiosynthesis and investigated their general utility. Each precursor was smoothly radiofluorinated (5 min) and the protecting soup at the 3-O-position was rapidly removed (1 min). The resulting rac-1,2-[F-18]FDAG was obtained in overall radiochemical yields of 20-30% (EOB) within 70 min including final preparative HPLC separation.

  DOI：

  10.1002/1099-1344(20001030)43:12<1159::aid-jlcr402>3.0.co;2-z

文献信息

• Furumoto; Nagata; Iwata, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S644-S645
  作者：Furumoto、Nagata、Iwata、Ido

  DOI：——

  日期：——
• Synthesis of 1-O-(8-[18F]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol for imaging intracellular signal transduction
  作者：Shozo Furumoto、Ren Iwata、Tatsuo Ido

  DOI：10.1002/1099-1344(20001030)43:12<1159::aid-jlcr402>3.0.co;2-z

  日期：2000.10.30

  An improved approach to the synthesis of 1-O-(8-[F-18]fluorooctanoyl)-2-O-palmitoyl-rac-glycerol (rac-1,2-[F-18]FDAG) has been developed. We designed and synthesized two new types of precursors for the radiosynthesis and investigated their general utility. Each precursor was smoothly radiofluorinated (5 min) and the protecting soup at the 3-O-position was rapidly removed (1 min). The resulting rac-1,2-[F-18]FDAG was obtained in overall radiochemical yields of 20-30% (EOB) within 70 min including final preparative HPLC separation.